Butyl isocyanate → HCID 23499245, compound

HRID 1836411Notes

Reaction equation

HRID 1836411 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([CH:7]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1)=[O:6].[CH2:17]([N:21]=[C:22]=[O:23])[CH2:18][CH2:19][CH3:20]>O1CCCC1>[CH2:17]([NH:21][C:22](=[O:23])[NH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([CH:7]1[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12]1)=[O:6])[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 8110Butyl isocyanate2×HCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 23499245HCID 23499245, compoundYield 121.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[3-aminobenzoyl]-1-methylpiperidine (25 mg, 0.115 mmol) and poly(4-vinyl pyridine) (50 mg, 0.400 mmol, 2% cross-linked) in tetrahydrofuran (2 mL) were allowed to stand 10 min. Butyl isocyanate (39 μL, 0.344 mmol) was added and the reaction mixture was mixed for 96 h at ambient temperature. An addition amount of butyl isocyanate(100 μL, 0.888 mmol) was added to the reaction mixture and mixing was continued for another 6 days. The reaction mixture was filtered and the filter cake was rinsed with methanol. Glacial acetic acid (0.5 mL) was added to the filtrate solution and the solution was mixed. This mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column. The column was rinsed extensively with methanol to remove impurities, then treated with a 2M ammonia in methanol to elute the product from the column. The solvent was evaporated to give 44.4 mg (>100%) of the title compound.

Workup

  1. additionthe reaction mixture was mixed for 96 h at ambient temperature
  2. additionmixing
  3. waitwas continued for another 6 days
  4. filtrationThe reaction mixture was filtered
  5. washthe filter cake was rinsed with methanol
  6. additionGlacial acetic acid (0.5 mL) was added to the filtrate solution
  7. additionthe solution was mixed
  8. additionThis mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column
  9. washThe column was rinsed extensively with methanol
  10. customto remove impurities
  11. additiontreated with a 2M ammonia in methanol
  12. washto elute the product from the column
  13. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7682a9c62f704d2bacc9c75a6b1ab925
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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